Anthony Gill targeted the first victim, a student, in the street when he pestered her before grabbing her and attempting to kiss her.
The 41-year-old then targeted a woman at Hartlepool Railway Station when he again grabbed the victim and kissed her after wrestling her to the ground.
Teesside Crown Court heard how Gill spent the day drinking before damaging three parked cars and attempting to steal alcohol from the loading bay of the town’s Asda store.
Annelise Haugstad, prosecuting, said Gill’s most serious offending happened when he targeted the two lone woman and sexually assaulted them.
Dealing with the first sexual assault, she said: “The defendant tried to engage her in conversation, he asked her if she wanted to hang around the area with him and she said no and felt uncomfortable.
“He started to call her pretty and then grabbed her arms, pulled her in towards him as he leaned into her face. She managed to break free and get away from him.”
Miss Haugstad said the second victim was attacked at the railway station where he dragged the woman to the floor before kissing her and saying – ‘this will be good for us’.
The court heard how before the sex assaults the defendant smashed car window as he wandered around Hartlepool town centre.
Gill, of no fixed abode, pleaded guilty to two charges of sexual assault, three charges of criminal damage and a further charge of attempted burglary in September last year.
Robert Mochrie, mitigating, said the defendant wished to apologise to both of the women for his behaviour now that he was sober.
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Judge Jo Kidd told Gill he had served the equivalent of an eight-month sentence whilst remanded in custody since his arrested as she passed a community order.
She said: “Your behaviour on that day was disgraceful, involving a number of different victims as you ranged around Hartlepool causing damage to whatever came in front of you, committing a low-level burglary and then pursuing the two women for a brief period.
“Your behaviour against both women was not sustained.”
Gill was made subject of a two-year community order to address his behaviour including a requirement to take part the Horizon Programme and attend 30 rehabilitation activity requirement days.